Asymmetric Diels-Alder reactions of cyclopentadiene in the synthesis of chiral norbornene derivatives

Mamedov, E. G.; Клабуновский, Е. И.

doi:10.1134/s1070428008080010

Cited by 20 publications

(9 citation statements)

References 79 publications

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“…[ 6 ] Indeed, such monomers are often based on norbornenes due to their stability, high reactivity, and easy preparation via Diels–Alder reactions. [ 7 ] The versatility of these monomers enables the preparation of a wide range of functional materials, such as highly conducting membranes or molecular carriers for drugs. [ 8 ] Peptide‐containing norbornenes are another example of functional monomers that are of particular interest as they carry the multifunctional character of the respective peptide, which is owed to the variety of natural and synthetic amino acids.…”

Section: Introductionmentioning

confidence: 99%

Ring‐Opening Metathesis Polymerization of Norbornene‐Based Monomers Obtained via the Passerini Three Component Reaction

Barther

Moatsou

2021

Macromol. Rapid Commun.

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Ring‐opening metathesis polymerization is a robust method to synthesize a variety of polymers by using ring‐strained molecules as monomers, e.g., norbornenes. However, the synthesis of monomers with multiple functional groups remains a challenge, albeit peptide functional norbornenes have previously been used. Here, the Passerini three component reaction is exploited to synthesize norbornenes with two variable functional groups varying in bulkiness and distance from the polymerizable alkene. The results indicate that the functional groups do not affect the kinetics of the polymerization, whereas the length of the linker has a minor effect. Furthermore, a diblock‐type copolymer is synthesized in a one‐pot fashion, also indicating good control of the polymerization process. The thermal properties of all polymers are evaluated, highlighting the effect of monomer composition. This synthetic approach can be transferred to a variety of compounds, thus promising highly diverse polymers with complex compositions and architectures.

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Section: Introductionmentioning

confidence: 99%

Ring‐Opening Metathesis Polymerization of Norbornene‐Based Monomers Obtained via the Passerini Three Component Reaction

Barther

Moatsou

2021

Macromol. Rapid Commun.

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“…Conjugated systems such as electron deficient alkenes and push‐pull alkenes are important reactants or intermediates in synthetic organic chemistry . Push‐pull systems also form a basis for the development of optical materials from organic molecules .…”

Section: Introductionmentioning

confidence: 99%

Electron Delocalization in Electron‐Deficient Alkenes and Push‐Pull Alkenes

Džambaski

Baranac‐Stojanović

2017

ChemistrySelect

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We have studied p electron delocalization in electron-deficient alkenes and push-pull alkenes by means of natural bond orbital analysis at the B3LYP/6-311 + G(d,p) level. The study revealed that the rarely mentioned p electron donation from an electron-accepting group (Acc) toward the C = C double bond in push-pull alkenes and electron-deficient alkenes can provide up to 10 % of total p electron stabilizing energy of a push-pull system and as much as 45 % in a strongly electron-deficient tetracyanoethene. The Acc ! C = C bond p electron donation is more intense in s-trans than in s-cis conformational arrangement, but is less dependent on Z/E isomerism in push-pull alkenes, being slightly more pronounced in Z isomers. Among different Acc substituents, CN and COOgroups contribute the largest percent of stabilizing energy and NO 2 the smallest. Increase in the number of Acc groups increases percentage contribution of Acc ! C = C bond p electron delocalization to a system stabilization. A difference in p* C = C orbital occupancy between isomers can be related with their chemical reactivity.[a] Dr.

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“…1 They are also employed as important monomers in ring-opening metathesis polymerizations (ROMP) for the synthesis of various polynorbornenes with high glass-transition temperatures, high light harvesting and liquid crystal properties, high optical clarity, and so on. 2,3 Norbornene moiety is normally constructed via Diels-Alder cycloaddition reaction, which represents the favorite protocol to synthesize sixmembered carbo-or heterocycles.…”

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confidence: 99%

“…Norbornene and its derivatives, which carry a double bond inducing significant ring strain and thus significant reactivity, can be utilized to make pharmaceutical intermediates, pesticide compounds, specialty fragrances, and in organic synthesis. 1 They are also employed as important monomers in ring-opening metathesis polymerizations (ROMP) for the synthesis of various polynorbornenes with high glass-transition temperatures, high light harvesting and liquid crystal properties, high optical clarity, and so on. 2,3 Norbornene moiety is normally constructed via Diels-Alder cycloaddition reaction, which represents the favorite protocol to synthesize sixmembered carbo-or heterocycles.…”

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confidence: 99%

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Mechanochemical Diels-Alder Cycloaddition Reactions for Straightforward Synthesis of endo-Norbornene Derivatives

Zhang¹,

Peng²,

Hao³

et al. 2010

Synlett

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Under mechanochemical milling conditions, DielsAlder cycloaddition of cyclopentadiene with maleic anhydride and maleimide derivatives proceeded very smoothly, affording endonorbornenes exclusively in quantitative yield. All the transformations were accomplished at room temperature without using any catalyst or organic solvent, thus the workup and purification procedure is very simple. Control experiments on traditional and other tentative conditions were also investigated.

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Asymmetric Diels-Alder reactions of cyclopentadiene in the synthesis of chiral norbornene derivatives

Cited by 20 publications

References 79 publications

Ring‐Opening Metathesis Polymerization of Norbornene‐Based Monomers Obtained via the Passerini Three Component Reaction

Ring‐Opening Metathesis Polymerization of Norbornene‐Based Monomers Obtained via the Passerini Three Component Reaction

Electron Delocalization in Electron‐Deficient Alkenes and Push‐Pull Alkenes

Mechanochemical Diels-Alder Cycloaddition Reactions for Straightforward Synthesis of endo-Norbornene Derivatives

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